Metal-Coordinated Water-Soluble Cavitands Act as C–H Oxidation Catalysts

Djernes, Katherine E.; Moshe, Orly; Mettry, Magi; Richards, Donald D.; Hooley, Richard J.

doi:10.1021/ol203243j

Cited by 26 publications

(20 citation statements)

References 33 publications

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“…39 When excess iron sulfate was added to solutions containing 28b, iron coordination was observed in the expected bidentate fashion, whereas 29a/b and 30a/b lacking the appropriate pyridyl geometry or containing only the phenyl group could not coordinate to the metal. 'Click' chemistry and saponification with Cs 2 CO 3 gave cavitands 28b, 29b, and 30b.…”

Section: Modifications At the Upper And Lower Rimsmentioning

confidence: 99%

Water-Soluble Cavitands ☆

Jordan

Gibb

2017

Comprehensive Supramolecular Chemistry II

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Section: Modifications At the Upper And Lower Rimsmentioning

confidence: 99%

Water-Soluble Cavitands ☆

Jordan

Gibb

2017

Comprehensive Supramolecular Chemistry II

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“…It is important to note the versatility of the azido cavitand IV for further functionalization via click chemistry highlighting the importance of straightforward synthesis for this type of cavitands. For instance, Hooley's group has published the synthesis of a compound similar to cavitand IV as precursor to advanced cavitands substituted with tri-azole groups which have been used as iron-coordinate water-soluble catalysts for C-H Oxidation [16]. Their method of synthesis consisted on using THF as a solvent mixed with a solution of NaN 3 in DMSO.…”

Section: Synthesis Of the Cavitand IVmentioning

confidence: 99%

Alternative and Eco-Friendly Synthesis of Tetrakis(Aminomethyl)Calix-[4]-Resorcinarene

Moussaoui¹,

Damaj²,

Wehbie³

et al. 2017

IJOC

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A cleaner and eco-friendly method was developed for the preparation of tetrakis(aminomethyl)calix-[4]-resorcinarene via a synthetic pathway of five steps starting from methylresorcinol. This alternative methodology is firstly based on avoiding the use of CH 2 BrCl, which is a non-eco-friendly substance with high ozone depletion potential, and on replacing it by CH 2 Cl 2 as a readily available reagent with much less dangerous effects. Secondly, this method engages acetone or CH 2 Cl 2 as the solvent of the bromination step in the place of the very toxic CCl 4 , leading to tetrakis(bromomethyl)calix-[4]-resorcinarene. The brominated intermediate has been reacted with sodium azide in acetone instead of the high-boiling solvent DMSO to produce tetrakis(azidomethyl) calix-[4]-resorcinarene without the need of tedious purification. Lastly, this work reports an efficient hydrogenation method of the versatile azido adduct employing Pt/C (5%) as the catalyst for the preparation of the amino cavitand as an alternative route with high atom economy that can replace the classical methods used currently.

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“…51 By positioning the catalytic groups on the ridge of concave surfaces, some ideal cavitand-based enzyme mimics can be generated. [130][131][132][133][134] For example, by positioning hydrogenbonding groups such as a dienophilic maleimide on the rim of cavitand, a rate acceleration of 60-fold was observed for the cycloaddition reaction between the maleimide and 9-anthracenemethanol. 135 Rebek and coworkers recently built a synthetic enzyme mimic 32 in which a deep and open-ended cavity was designed (Fig.…”

Section: Container Molecules As Artificial Enzymesmentioning

confidence: 99%

Artificial enzymes based on supramolecular scaffolds

2012

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Enzymes are nanometer-sized molecules with three-dimensional structures created by the folding and self-assembly of polymeric chain-like components through supramolecular interactions. They are capable of performing catalytic functions usually accompanied by a variety of conformational states. The conformational diversities and complexities of natural enzymes exerted in catalysis seriously restrict the detailed understanding of enzymatic mechanisms in molecular terms. A supramolecular viewpoint is undoubtedly helpful in understanding the principle of enzyme catalysis. The emergence of supramolecular artificial enzymes therefore provides an alternative way to approach the structural complexity and thus to unravel the mystery of enzyme catalysis. This critical review covers the recent development of artificial enzymes designed based on supramolecular scaffolds ranging from the synthetic macrocycles to self-assembled nanometer-sized objects. Such findings are anticipated to facilitate the design of supramolecular artificial enzymes as well as their potential uses in important fields, such as manufacturing and food industries, environmental biosensors, pharmaceutics and so on.

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Metal-Coordinated Water-Soluble Cavitands Act as C–H Oxidation Catalysts

Cited by 26 publications

References 33 publications

Water-Soluble Cavitands ☆

Water-Soluble Cavitands ☆

Alternative and Eco-Friendly Synthesis of Tetrakis(Aminomethyl)Calix-[4]-Resorcinarene

Artificial enzymes based on supramolecular scaffolds

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